


scotch on the rocks

by taffeta



Category: The Simpsons
Genre: Drag queen waylon, Drinking, M/M, Men in drag, Mentions of Drunk Driving, Mentions of passing as female, Sexual Tension, The gay club across the street as mentioned in Flaming Moe’s, Two weird old men in love MY BRAND, mentions of smoking, moe is stupid thirsty, mr burns mentioned in passing cause i hate capitalists and i hate their relationship, set after flaming Moe and werking mom, the mysterious waylon
Language: English
Status: Completed
Published: 2020-10-26
Updated: 2020-10-26
Packaged: 2021-03-08 17:54:03
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,735
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27200720
Author URL: https://archiveofourown.org/users/taffeta/pseuds/taffeta
Summary: The Mysterious Waylon heads to an empty Moe’s Tavern after a long night in drag. On the same night, Moe meets the most beautiful woman he’s ever seen, and these two events don’t overlap in any way whatsoever.
Relationships: Waylon Smithers/Moe Szyslak
Comments: 6
Kudos: 31





	scotch on the rocks

Waylon, feeling absolutely anything but mysterious at this point in the night, tugged at the left thigh high lace stocking…again, as he headed out. The damn thing had been rolling down in the back all night, even with the garter. God help him, he looked great, but at the cost of having to pull up his accessories all night? 

“That’s what you get for ordering cheap and quick.” he muttered to himself, righting his lopsided tiddies underneath the thin top.

Waylon stumbled outside, leaving the conflicting smells and terribly loud, grating club music of the bar behind, and the bouncer blew him a kiss—“come back soon, baby!”—before the door slammed shut behind him, seemingly with no signs of slowing down like he quickly was. Hoots and excited cries, muffled by the closed door really helped to punctuate the silent stillness of three thirty, AM, in a small town like Springfield, and Waylon began to feel whatever confidence he’d had, dancing with his fellow men and queens drain out of him. 

It was cold, and sometime between the hours of eleven at night to now it had drizzled; shiny wet pavement reflected the overhead streetlights, as he wrapped his arms around himself, and took a step foreword towards the lot. Waylon’s black kitten heels clicked over the sidewalk as he moved, and once again he found his fingers pulling at the black stocking on the left, grunting in frustration. That was the last time he would order from one of those knockoff websites. 

A light flickered from the corner of his vision, and he stopped to look, compelled by some unknown force; of course, there stood, as it had for the past thirty some-odd years, Moe’s Tavern. The local hovel for any and every man in this town who took spirits with a little too much excess, the same place he’d successfully converted into an upscale bar with a...more agreeable crowd, before Moe turned it back into the shithole it was. 

Regardless, the sight provided Waylon with a fraction of comfort, especially since he wasn’t quite ready to call the night quits, but he wasn’t shelling out fifteen dollars for a frou frou pink drink served in an oversized fishbowl. Inadvertently, he craned his head to the left and right to look both ways across the street, before crossing to the other side. Like there were any cars out here at this hour. 

Waylon swung the door open to Moe’s, nearly tripping over the doorway between the bar and the street, before righting himself. There was no way he was that drunk, not from anything that contained so much sugar it made his stomach queasy, but the heels were hard to navigate in, especially after a long night of grinding. 

“Honey, I’m home,” Waylon giggled to himself, as the doleful sounds of Stevie Nicks floated from the radio into the empty bar. He slid onto one of the barstools, and the prosthetic tits he’d ordered custom made brushed up so close against the counter that he had to move the seat away a bit. Oh well, he thought to himself, adjusting the black, spaghetti strap leather top so it covered his boobs, such is a price you pay for beauty.

The town drunk (Barney, maybe?) sat at the end of the L shape, slumped down with his shoulders rising and falling every few seconds. He didn’t look up upon the arrival of some other customer this late at night. Waylon could practically smell the man from here; though, thankfully, Barney tended to leave the other clients in peace, and sometimes he was good for a laugh when he was conscious and able to form words without stumbling over himself too terribly. Waylon reached for a peanut in one of the nearby bowls, and then thought better of it. 

“I’m about five minutes from closing,” finally, a voice with all the gentleness of sandpaper grating on a chalkboard cut through the haunting tunes of Fleetwood Mac, the steps of slightly heeled feet clicking against the bar floors, “order what youse want now, before I throw your sorry ass out to the curb—“

Moe rounded the corner, rubbing the inside of a glass cleaned with a rag that Waylon hoped wasn’t his multi purpose bar rag. They’d had a whole discussion on cleanliness practices and standards and even if it wasn’t technically his bar anymore, Smithers balked at the idea of drinking from a filthy, streak stained cup. 

“Thank god, Moe,” he started, his own voice not a picture of softness either when it came out of his mouth raspy and hoarse, “scotch on the rocks, if you got it. What a night I’ve had.”

Waylon let his own head rest against the bar for a second, a spitting image of Barney on the other end, and in the darkness of his forehead pressed against the counter, the sound of a low whistle filled his ears, as close to him as it was confusing. Waylon raised his head, and nearly fell off the stool; because there was Moe, right in front of him, with a tall glass of what was presumably scotch set in reaching distance. Waylon startled, and Moe slicked back whatever grease he’d plopped on his head to keep his hair in place. 

“One scotch, for one beautiful woman,” the bartender pushed the glass closer so Waylon could get at it, leaning against the bar with one elbow, “don’t think we’ve met before, cause I would’ve remembered a set of legs like yours, toots.”

Waylon was floored. The only sound that escaped his lipstick lined mouth (revlon colorstay in cocoawine, thank you very much) was an incredulous, low chuckle, more of a release of air that made his chest bounce instead of a laugh. He knew he looked fairly fish, passing enough for a woman that he’d even gotten a handful of comments from the club across the street (“lesbian bar’s over there, lady”) until he opened his mouth and they got an earful of his usually deadpan, always low voice—but Waylon hadn’t thought he’d passed _that_ well, well enough where Moe didn’t recognize him whatsoever. It almost made him feel mildly flattered— _very_ flattered, he corrected himself, as Moe sent a wink his way, before reaching behind him and pouring himself a shot of whiskey which he sat side by side with Waylon’s drink—but he was in the mood for hard alcohol after a long night, not for throwing on his fishiest, most feminine voice and stepping into his drag persona like a suit. 

“Uh,” Waylon cleared his throat, “Moe—“

“Did I come on a little too strong there?” The bartender hissed through his teeth in embarrassment, knocking his palm softly against his temple, mouth pressed in a line, “Stupid, stupid—I tend to do that sometimes. I get the sense that the ladies aren’t much in favor for it, but you haven’t slapped me with a purse yet or called the cops, so I’m gonna try that again.”

Moe made no comment about Waylon’s deep, masculine voice; Waylon doubted very much if he’d even paid any sort of attention to it, and watched the show play out in front of him without a word as Moe downed the shot in one swoop, poured himself another, and downed that one in a matter of seconds. He burped, and at least had the decency to cover it with the side of his arm, though Waylon still recoiled as the smell drifted his way.

“‘Know what they say, doll: “liquor is quicker”. Enough about me, though,” Moe leaned over again, and Waylon found himself a little torn on what to do next; on one hand, he found Moe attractive in a strange sort of way, a kind soul in the body of a man that was kind of weird and always carried a palpable stink on him, that smelled like body odor and stale cigs; on the other hand, he felt a little strange tricking this man who Waylon considered a friend into thinking he was this mysterious, pretty woman who haunted bars at four AM and seduced lonely bartenders, and despite himself, Waylon didn’t quite lean all the way back, not close enough for kissing distance, but enough so Moe could, tentatively, place his fingers on Waylon’s manicured hand, and Waylon almost flinched. Jesus, Moe’s hands were cold. 

“What about you? Youse from around here?” Moe asked, hopefully, and Waylon sucked in his teeth.

“I suppose, but—“

“Again, I definitely would’ve remembered a dame like youse shuffling through my doors once in a while,” Moe offered, “got a boyfriend? A husband, maybe? Hey, even a girlfriend, I’m flexible—“

Alright. Waylon snatched his fingers away, flinging the bowler hat from his head as if it would reveal his true identity, and grabbed Moe by the shoulders.

“Moe, it’s me! It’s _Smithers_!” 

“I—Waylon?” Moe didn’t look too upset, thank god; if anything, the way his brows were drawn together, and the middle of his forehead creased as he tried to process this new information, he simply looked extremely, utterly confused. As if Waylon had confided in him the cosmic secrets of the universe, or tried to explain the mechanisms of quantum theory. Like he literally couldn’t believe this was his ex-boss.

“That’s you under there?” A hands on rather than a visual learner, Moe reached out and took a curl from Waylon’s head of hair in his fingers, and to Smithers’ surprise, yanked it up, hard enough to make him gasp.

“Ow! What the hell, Moe!”

“That’s your real hair?!” Moe whistled lowly, clearly impressed, “a queen who doesn’t wear a wig?”

Waylon rubbed his scalp, “I prefer the short and natural look. Plus, it gets hot after a while, especially after a long night of selling tubberwear.” He joked, but Moe made no notice of it, instead trailing his roaming eyes down to Waylon’s chest.

“And these?” Once again, his grabby hands reached out to the top of Waylon’s right prosthetic boob, pinching at the fatty flesh there, “these are definitely fake, I probably woulda remembered you walking around with these bad boys.”

Waylon slapped his hand away, trying to fight off the smile forming itself on his face, “Yeah, they’re for the look, but that doesn’t mean you can touch. Next time you pinch me like that, I’m charging ten dollars.” 

Moe retracted his arm, laughing, “Got it, got it. I’ll keep these roving mitts to myself,” he looked Waylon up and down, at least the parts of his body that he could see above the bar, one eyebrow raised in something Smithers couldn’t read, “you look good as a woman, Waylon.” 

Smithers sipped at his drink; it had been sitting there for so long that much of the ice evaporated, leaving a ring along the wood of the bar.

“I try,” he said, winking conspiratorially at Moe, batting his fake eyelashes in a mockingly flirtatious move, that only seemed to make Moe look even more flustered. 

“Like...really, really good.” Moe conceded, his face flushed, rubbing at the back of his head and looking around the empty establishment like he didn’t know where to settle his eyes, “like, ‘I don’t even mind you’re a man’ good.”

“...thanks.” The vibe changed immediately, from friendly camaraderie into a weird sort-of tension that Waylon certainly had a name for but didn’t want to speak into reality, in case he was reading anything wrong. The way Moe kept darting his eyes though, from Waylon’s chest to his lips, back over to something in the background, made Waylon almost ninety-eight percent positive that the mood was exactly what he thought.

Ah, fuck it. What was the point of being a drag queen if he didn’t put on a good show?

Waylon trailed his fingers over the drink glass, playing with the fat drops of condensation as the travelled along the rim to the base, using his press on nails, making a point not to look at Moe as he stroked the cup. Near him, over the soft Carpender’s song that played, Waylon heard him take a deep intake of breath through his nose, and darted his eyes toward the bartender. Moe looked away, a very light redness showing on his cheeks. 

“You want to know my drag name?” Waylon asked him softly, raising himself out from the stool so his elbows held most of his weight, and his legs were pressed together on the rickety cushion, leaning over the bar, over Moe, whose blush had grown but who made no move to step away.

“I—yeah, yeah, sure?” He breathed. Unsure what to do with his hands at the moment, Moe kept them almost rigidly straight against his sides, and Waylon grinned down at him.

“They call me, The Mysterious Waylon.” Waylon leaned forward, whispering the answer against the shell of Moe’s ear, ghosting his lips against the skin there, which earned Waylon another deep, shaky breath from the other man.

“Why do they, uh, c-call you that?”

Waylon pressed his forehead against Moe’s, and this time the bartender’s hands shot up, grabbing Smithers by the middle, wrapping his arms against the small of Waylon’s back as Waylon initiated the kiss, pressing his closed mouth to Moe’s chapped lips. Immediately, Moe eased open his mouth, and Waylon was pleasantly surprised to find the taste of coffee and whiskey and the smoky aftertaste of cigarettes against his own tongue, exploring the craters and gaps in Moe’s mouth as he ran it over the bartender’s teeth.

Grunting, Moe slithered one hand from his waist to the back of Smithers’ head, trying to pull them even closer, nearly resulting in Waylon falling over as he lost balance on the rickety stool, and he balanced himself on Moe’s shoulders, feeling the soft hair on the back of his head as they kissed, reveling in the high whistle of Moe’s breath coming out through his nose.

Waylon broke first; just as Moe was running himself against the roof of his mouth, trying to shove his tongue in the back of Waylon’s throat. He wiped a line of drool from the corner of his mouth, keeping the back of his hand to hide his smile, as he looked at Moe’s face; the man looked thoroughly hot and bothered, the blush having spread from his cheeks all the way down to the visible skin of his throat. A thin, thin sweat glimmered on his forehead, visible even with the dank bar lighting, and Waylon leaned back, righting himself. When he jumped from the stool, his heels clicked on the floor. 

“Thanks, Moe,” Waylon raised his hand in goodbye; the other was poised on the door handle, ready to swing it open and venture into the night, satisfied, “drink’s on the house, right?”

Within the seconds afterward, he’d regained at least some of his sense; Moe cleared his throat, arms folded over the counter, smiling at Waylon lopsidedly.

“Baby, you keep comin’ dressed like that and everything’s on the house.” he winked back, “especially me.”

With a coquettish grin of his own, Waylon batted his lashes once more, and blew Moe a kiss goodbye, before disappearing into the cool air of an early Friday morning, hitting the pavement fast before any early-riser Springfieldites caught him looking like this. The lights in the club across the street had gone out completely, no doubt in preparation for a bustling Friday night, and Waylon fished his car keys out of his pocket, rounding the corner into the car lot behind the building. He wasn’t remotely close to drunk, but nevertheless, he slid into the front seat, nursing an iced coffee from the night before that had been kept cold by the temperature; but it was probably in everyone’s best interest for him to wait a couple minutes for the coffee to sober him up before heading back home. Reports were waiting on his desk from Monty, and he was in no rush to look them over.

Instead, Waylon sat there in the relative darkness of his car, the only light coming from the moon and a nearby street lamp, playing with the skin on his lips, and wondering to himself what day and when, he’d head back to Moe’s place. Next time, he thought, pulling the stocking up one last time, no fucking garters.

**Author's Note:**

> Might make a second chapter who knowsss
> 
> Love these nasty old men


End file.
